title: Versatile construction of functionalized tropane ring systems based on lactam activation: enantioselective synthesis of (+)-pervilleine B.
abstract: The halo-assisted intramolecular addition of silyl enol ethers with in situ activated lactams yielded (hydroxylated) 1-halo-8-azabicyclo[3,2,1]octane and 1-halo-9-azabicyclo[3,3,1]nonane ring systems, which provided an easy enantioselective access to 6β-silyloxytropane-3-one, 3α,6β-dihydroxytropane, and pervilleine B. The absolute configuration of the natural (-)-pervilleine B was determined to be 1R,3R,5S,6R.
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, and Fujian Provincial Key Laboratory of Chemical Biology, Xiamen University, Xiamen, Fujian 361005, China.
authors.forename: Su-Yu
authors.initials: SY
authors.lastname: Huang
authors.forename: Zong
authors.initials: Z
authors.lastname: Chang
authors.forename: Shi-Chuan
authors.initials: SC
authors.lastname: Tuo
authors.forename: Long-Hui
authors.initials: LH
authors.lastname: Gao
authors.forename: Ai-E
authors.initials: AE
authors.lastname: Wang
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D053961:Azabicyclo Compounds / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D008968:Molecular Conformation; D012825:Silicon / Q000737:chemistry; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D053961:Azabicyclo Compounds; D007769:Lactams; D014326:Tropanes; C467799:pervilleine B; D012825:Silicon